#------------------------------------------------------------------------------
#$Date: 2020-12-04 08:04:18 +0200 (Fri, 04 Dec 2020) $
#$Revision: 259535 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/32/4113219.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4113219
loop_
_publ_author_name
'Hyunsik Moon'
'Roswitha Zeis'
'Evert-Jan Borkent'
'Celine Besnard'
'Andrew J. Lovinger'
'Theo Siegrist'
'Christian Kloc'
'Zhenan Bao'
_publ_contact_author_email       celine.besnard@materialkemi.lth.se
_publ_contact_author_name        'celine Besnard'
_publ_section_title
;
 Synthesis, Crystal Structure, and Transistor Performance of Tetracene
 Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15322
_journal_page_last               15323
_journal_paper_doi               10.1021/ja045208p
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C18 H10 Cl2'
_chemical_formula_sum            'C18 H10 Cl2'
_chemical_formula_weight         297.16
_chemical_name_common            'trans di-chloro tetracene'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.37(3)
_cell_angle_beta                 92.02(2)
_cell_angle_gamma                99.47(3)
_cell_formula_units_Z            2
_cell_length_a                   3.8607(12)
_cell_length_b                   8.664(3)
_cell_length_c                   19.686(5)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55
_cell_measurement_theta_min      1
_cell_volume                     647.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_av_sigmaI/netI    0.3298
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5777
_diffrn_reflns_theta_full        27.64
_diffrn_reflns_theta_max         27.64
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.485
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
  the absorption correction
 based on the crystal shape
 was made in the program excalibur by Oxford diffraction
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       platelet
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.713
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.713
_refine_ls_R_factor_all          0.2283
_refine_ls_R_factor_gt           0.0534
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1925
_reflns_number_gt                733
_reflns_number_total             2793
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja045208psi20040809_125857.cif
_cod_data_source_block           new
_cod_depositor_comments
;

2020-12-03
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H20 Cl4'
_cod_original_formula_weight         594.32
_cod_original_formula_moiety         'C18 H10 Cl2,C18 H10 Cl2'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        647.7(4)
_cod_database_code               4113219
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.2800(5) -0.17589(19) 1.63451(8) 0.0498(6) Uani 1 1 d .
Cl2 Cl -0.0779(5) 0.1159(2) 0.84079(8) 0.0618(7) Uani 1 1 d .
C7 C 0.2110(16) -0.0226(7) 1.5849(3) 0.0326(16) Uani 1 1 d .
C12 C -0.0256(16) 0.0649(7) 1.4785(3) 0.0315(15) Uani 1 1 d .
C15 C 0.4071(17) 0.4119(8) 1.5904(3) 0.0388(17) Uani 1 1 d .
H15 H 0.3686 0.4930 1.5636 0.047 Uiso 1 1 calc R
C16 C 0.3357(16) 0.1291(8) 1.6100(3) 0.0326(15) Uani 1 1 d .
C19 C 0.1032(16) 0.2194(7) 1.5038(3) 0.0352(17) Uani 1 1 d .
H19 H 0.0693 0.3015 1.4773 0.042 Uiso 1 1 calc R
C22 C 0.1611(16) -0.2493(8) 0.9417(3) 0.0391(17) Uani 1 1 d .
C23 C 0.5832(18) 0.4462(8) 1.6506(3) 0.0468(19) Uani 1 1 d .
H23 H 0.6716 0.5501 1.6645 0.056 Uiso 1 1 calc R
C25 C -0.0949(16) 0.1501(8) 1.1131(3) 0.0419(19) Uani 1 1 d .
C26 C 0.0347(17) -0.0512(8) 1.0273(3) 0.0368(16) Uani 1 1 d .
C27 C 0.2508(17) -0.3977(8) 0.9241(4) 0.049(2) Uani 1 1 d .
H27 H 0.2883 -0.4633 0.9584 0.059 Uiso 1 1 calc R
C30 C 0.6367(18) 0.3229(9) 1.6942(3) 0.049(2) Uani 1 1 d .
H30 H 0.7530 0.3487 1.7365 0.059 Uiso 1 1 calc R
C31 C 0.222(2) -0.3466(10) 0.8055(4) 0.064(2) Uani 1 1 d .
H31 H 0.2494 -0.3807 0.7606 0.077 Uiso 1 1 calc R
C33 C 0.5203(18) 0.1705(8) 1.6744(3) 0.0447(18) Uani 1 1 d .
H33 H 0.5604 0.0924 1.7027 0.054 Uiso 1 1 calc R
C34 C 0.283(2) -0.4461(9) 0.8590(4) 0.063(2) Uani 1 1 d .
H34 H 0.3446 -0.5438 0.8486 0.076 Uiso 1 1 calc R
C35 C 0.2771(16) 0.2537(8) 1.5662(3) 0.0351(17) Uani 1 1 d .
C36 C 0.1277(17) -0.1981(8) 1.0089(3) 0.0439(18) Uani 1 1 d .
H36 H 0.1684 -0.2633 1.0432 0.053 Uiso 1 1 calc R
C38 C 0.0012(18) -0.0049(8) 0.9052(3) 0.0444(18) Uani 1 1 d .
C39 C 0.1281(19) -0.2060(9) 0.8185(3) 0.055(2) Uani 1 1 d .
H39 H 0.0845 -0.1452 0.7828 0.066 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C16 C7 C12 124.9(5) . 2_558
C16 C7 Cl1 118.5(4) . .
C12 C7 Cl1 116.6(5) 2_558 .
C19 C12 C7 124.8(5) . 2_558
C19 C12 C12 118.4(7) . 2_558
C7 C12 C12 116.7(7) 2_558 2_558
C23 C15 C35 121.5(6) . .
C7 C16 C33 124.4(6) . .
C7 C16 C35 116.6(5) . .
C33 C16 C35 119.0(6) . .
C35 C19 C12 122.4(6) . .
C36 C22 C27 121.9(6) . .
C36 C22 C25 119.9(6) . 2_557
C27 C22 C25 118.2(6) . 2_557
C15 C23 C30 120.4(7) . .
C38 C25 C39 123.9(7) 2_557 2_557
C38 C25 C22 117.4(6) 2_557 2_557
C39 C25 C22 118.7(7) 2_557 2_557
C38 C26 C36 124.2(6) 2_557 .
C38 C26 C26 117.1(8) 2_557 2_557
C36 C26 C26 118.6(7) . 2_557
C34 C27 C22 121.5(7) . .
C33 C30 C23 121.0(6) . .
C39 C31 C34 121.9(7) . .
C30 C33 C16 120.1(6) . .
C27 C34 C31 119.9(7) . .
C19 C35 C15 121.1(6) . .
C19 C35 C16 120.9(6) . .
C15 C35 C16 117.9(6) . .
C22 C36 C26 122.6(6) . .
C25 C38 C26 124.4(6) 2_557 2_557
C25 C38 Cl2 118.3(5) 2_557 .
C26 C38 Cl2 117.3(5) 2_557 .
C31 C39 C25 119.9(7) . 2_557
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C7 1.743(6) .
Cl2 C38 1.742(6) .
C7 C16 1.380(8) .
C7 C12 1.416(8) 2_558
C12 C19 1.405(8) .
C12 C7 1.416(8) 2_558
C12 C12 1.480(11) 2_558
C15 C23 1.339(8) .
C15 C35 1.427(8) .
C16 C33 1.429(8) .
C16 C35 1.461(8) .
C19 C35 1.371(8) .
C22 C36 1.388(8) .
C22 C27 1.413(8) .
C22 C25 1.460(9) 2_557
C23 C30 1.445(9) .
C25 C38 1.396(8) 2_557
C25 C39 1.421(8) 2_557
C25 C22 1.460(9) 2_557
C26 C38 1.407(8) 2_557
C26 C36 1.409(8) .
C26 C26 1.478(11) 2_557
C27 C34 1.340(8) .
C30 C33 1.353(8) .
C31 C39 1.341(10) .
C31 C34 1.436(10) .
C38 C25 1.396(8) 2_557
C38 C26 1.407(8) 2_557
C39 C25 1.421(8) 2_557
